Water → 4-[1-(Diphenylmethyl)azetidin-3-yl]morpholine
Reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.O>C(#N)C>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Procedure
A solution of 1-diphenylmethyl-3-methanesulphonyloxyazetidine (see Preparation 54) (24.46 g, 7.72 mmol), potassium carbonate (32 g, 3 mol. equiv.) and morpholine (7.34 ml, 1.09 mol. equiv.) in acetonitrile (200 ml) was heated under reflux for four hours. The solution was then cooled to room temperature, water (50 ml) added and the mixture concentrated under reduced pressure. The residue was partitioned between ethyl acetate (400 ml) and water (400 ml) and the organic phase separated and washed with water (2×400 ml). The organic phase was dried over magnesium sulphate, filtered and the solvent removed from the filtrate under reduced pressure. The residue was then chromatographed using silica gel eluting with hexane:diethyl ether (1:1, by volume) to give the title compound (16.5 g).
Workup
- temperatureunder reflux for four hours
- concentrationthe mixture concentrated under reduced pressure
- customThe residue was partitioned between ethyl acetate (400 ml) and water (400 ml)
- customthe organic phase separated
- washwashed with water (2×400 ml)
- dry with materialThe organic phase was dried over magnesium sulphate
- filtrationfiltered
- customthe solvent removed from the filtrate under reduced pressure
- customThe residue was then chromatographed
Sources & evidence
- ORD record
- ord-9b323fc69acd4a1b8480978216809ff0
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05968923
Reaction notes
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